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Table 1 HR-MS data for primaquine and its metabolites from human plasma and urine samples

From: Metabolism of primaquine in normal human volunteers: investigation of phase I and phase II metabolites from plasma and urine using ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry

# RT (min) Exact mass Peaka [M + H]+ Molecular Formula Biotransformation (Metabolite Predicted/Identified) Sample/source
1 3.5 273.1477 274.1549 (274.1550) C15H19N3O2 Hydroxylation and quinone-imine formation Plasma/urine
2 4.97 259.1679 260.1769 (260.1757) C15H21N3O Precursor ion (PQ)
3 5.3 256.1206 257.1273 (257.1285) C15H16N2O2 Oxidative deamination to acid + cyclization (Carboxyprimaquine lactam)
4 7.98 479.1898 480.1992 (480.1977) C22H29N3O9 Carbamoyl glucuronide formation (PQ-N-carbamoyl-glucuronide conjugate)
5 8.95 274.1312 275.1385 (275.1390) C15H18N2O3 Deamination + Acid (Carboxyprimaquine)
6 10.12 288.1468 289.1560 (289.1547) C16H20N2O3 Deamination + Acid + Methylation (Carboxyprimaquine methyl ester)
7 4.67 421.2207 422.2315 (422.2286) C21H31N3O6 Glucose conjugation Plasma
8 6.03 320.1367 321.1454 (321.1445) C16H20N2O5 (Deamindation + acid) + 2xOH + methylation (dihydroxy carboxyprimaquine methyl ester)
9 9.65 317.1734 318.1789 (318.1812) C17H23N3O3 Methyl carbamate formation (PQ methyl carbamate)
10 1.78 259.1315 260.1403 (260.1399)* C14H17N3O2 5-Hydroxylation +Orthoquinone formation (5,6 orthoquinone primaquine) Urine
11 1.9 451.1955 452.2011 (452.2027) C21H29N3O8 Hydroxylation + Glucuronide conjugation
12 2.2 421.1849 422.1908 (422.1922) C20H27N3O7 5-Demethylation + Glucuronidation (5-desmethyl PQ glucuronide)
13 2.32 451.1955 452.2011 (452.2027) C21H29N3O8 Hydroxylation + Glucuronide conjugation
14 2.34 275.1634 276.1712 (276.1707) C15H21N3O2 Hydroxylation (4-OH PQ)
15 3.1 452.1795 453.1881 (453.1868) C21H28N2O9 Deamination + alcohol + hydroxylation + glucuronidation
16 3.12 315.1947 316.2002 (316.2020) C18H25N3O2 Methylation + Acetylation
17 3.45 275.1634 276.1694 (276.1707) C15H21N3O2 Hydroxylation
18 3.85 275.1634 276.1697 (276.1707) C15H21N3O2 Hydroxylation (2-OH PQ)
19 4.43 245.1528 246.1617 (246.1601) C14H19N3O Demethylation
20 4.88 493.206 494.2127 (494.2133) C23H31N3O9 Acetylation + (Hydroxylation + Glucuronide conjugation)
21 4.92 275.1634 276.1705 (276.1707) C15H21N3O2 Hydroxylation (3-OH PQ)
22 5.18 273.1477 274.1534 (274.1550) C15H19N3O2 Hydroxylation and quinone-imine formation
23 5.67 483.1853 484.1932 (484.1926) C21H29N3O10 3 x Hydroxylation + 1 x glucuronide conjugation
24 5.9 289.1426 290.1500 (290.1499) C15H19N3O3 2 x Hydroxylation + quinone-imine formation
25 5.92 291.1583 292.1647 (292.1656) C15H21N3O3 2 x hydroxylation
26 6.15 498.1486 499.1545 (499.1559) C21H26N2O12 Deamination + acid + 3 x hydroxylation + 1 x glucuronide conjugate
27 6.17 466.1587 467.1666 (467.1660) C21H26N2O10 (Hydroxylation + glucuronide conjugation) + (deamination + acid)
28 6.4 291.1583 292.1647 (292.1656) C15H21N3O3 2 x hydroxylation
29 7.27 301.179 302.1875 (302.1863) C17H23N3O2 Acetylation
30 7.6 435.2006 436.2100 (436.2078) C21H29N3O7 Glucuronide conjugation
31 7.74 436.1846 437.1909 (437.1918) C21H28N2O8 Oxidative deamination to alcohol + glucuronide conjugation
32 7.79 450.1638 451.1714 (451.1711) C21H26N2O9 (Deamination + acid) + glucuronide conjugation
33 8.2 276.1474 277.1552 (277.1547) C15H20N2O3 Deamination + alcohol + hydroxylation
34 8.6 435.2006 436.2100 (436.2078) C21H29N3O7 Glucuronide conjugation
35 8.65 315.1583 316.1676 (316.1656) C17H21N3O3 Acetylation + hydroxylation + quinone-imine formation
36 10.38 302.1267 303.1324 (303.1339) C16H18N2O4 Deamination + acid + methylation + hydroxylation + quinone-imine formation
  1. aObserved mass of the metabolite (calculated mass is shown in parenthesis)